When is good enough actually good enough? AI is reshaping how I work and live. And a member with a portfolio that's beaten an all-in-one Vanguard LifeStrategy fund for ten years asks whether the complexity is worth it — or whether it's time to simplify. Show Notes The Upswing: How We Came Together a Century Ago and How We Can Do It Again by Robert Putnam—Simon &Schuster An update on our model deprecation commitments for Claude Opus 3—Anthropic Claude's … [Read more...]
548: What Will Drive Financial Markets in 2026—and How to Make It Your Best Year
We explore the forces likely to shape financial markets in 2026 and how to make better decisions as you pursue your goals this year. Topics covered include: The difference between intentions and resolutions Key behavioral biases and how to overcome them The cautionary tale of a private real estate fund that went public Is the affordability crisis real? The big test for AI in 2026 The financial and economic outlook for the year Show Notes A Slightly Better You … [Read more...]
542: Don’t Take Financial Advice from AI
A concerning example of how AI makes simple financial mistakes, and the right and wrong way to use AI to make financial decisions. Topics covered include: How AI ignores the time value of money A detailed example of ChatGPT misleading by making a simple math mistake Some examples of opportunity costs and sunk costs when making financial decisions Understanding how AI works can help us use it more effectively Show Notes What Kind of a “PhD-level Expert” Is ChatGPT … [Read more...]
538: Forests, Fakes, and the Fight for the Real
From salmon leaping along the Vancouver Island coast to fake bands on Spotify, this episode explores the divide between the physical and digital economy, and what lumber markets, managed forests, and everyday life teach us about staying connected to the real. Topics covered include: How timber investing works and why it is reflective of how industries evolve What percent of economic output is physical versus digital, and how has that changed over the past fifty years How … [Read more...]
536: How to Invest During a Bubble?
From the dot-com boom to today’s AI frenzy, bubbles follow a familiar script. This episode explores how to recognize them, what sustains them, and how to position your portfolio without getting swept up in the hype. Topics covered include: How U.S. stock markets are the most concentrated and most expensive of all time What constitutes a bubble and what sustains it How to invest during a bubble Changes David recently made in his portfolio in response to the AI … [Read more...]
535: Six Principles for Thriving Under Uncertainty and How Big Tech Is Doing the Opposite
A practical framework for making better decisions, managing risk, and finding opportunity in unpredictable environments. We contrast these principles with the massive $2.9 trillion AI data center build-out by Big Tech, which is betting big on a single superintelligence future. Show Notes Inside the relentless race for AI capacity—The Financial Times Inside the AI race: can data centres ever truly be green?—The Financial Times The Kanye/Data Center Crossover by Paul … [Read more...]
507: Where You Live Matters – How Geography Contributes to Wealth
How geography contributes to economic growth and can increase or lower the cost of living. Topics covered include:Why living in a developing country like Costa Rica is still relatively expensiveHow Amazon and e-commerce platforms lower the cost of livingWhy we should consider slowing down our rate of consumptionHow geography is impacting the rollout of AI Show Notes Market Research in Costa Rica: Costa Rica is a strong market in Central America providing many benefits.—SIS … [Read more...]
505: Optimization, AI, and Opting Out with Coco Krumme
In our final episode of the year, I converse with author and data scientist Coco Krumme about the benefits and costs of optimization in finance, industry, and our daily lives. We explore AI and its overlap with optimization. We also consider the pros and cons of life optimization and finally discuss the extreme challenge of opting out. Show Notes Optimal Illusions: The False Promise of Optimization by Coco Krumme—Penguin Random House cocofolio.com Coco … [Read more...]
457: AI’s Fork in the Road: Societal Bliss or Existential Threat
One year after the release of ChatGPT, we explore the positive and negative paths AI could take and what individuals can do to assist with a positive outcome. Topics covered include: How David uses AI to increase his personal productivity The societal and economic impacts of AI, including its potential to enhance corporate profitability and individual productivity Changes at OpenAI's executive level are examined, highlighting a shift in the organization's direction and … [Read more...]
439 Plus: New Portfolio Trades, Market Temperature, Providing Investment Help, and TFLO
In Plus episode 439, we continue discussing AI large-language models and how to think about them. David shares two AI-influenced trades in his portfolio. We review a recent editorial by Howard Marks on market timing and the market's temperature. We discuss how to help family members and friends with investment-related challenges. Finally, we discuss how ETF and mutual fund distributions impact the price, using TFLO as an example. … [Read more...]
